1-Butanol → HCID 178450849, compound

HRID 1481193Notes

Reaction equation

HRID 1481193 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])=[CH:8][CH:9]=2)[C:4](=[O:19])[N:3]1[CH2:20][C:21]([O:23][CH3:24])=[O:22].[CH2:25](O)[CH2:26][CH2:27]C>CCOC(C)=O>[OH:1][C:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])=[CH:8][CH:9]=2)[C:4]([OH:19])=[C:20]([C:21]([O:23][CH2:24][CH2:25][CH2:26][CH3:27])=[O:22])[N:3]=1

Participants

4

Reactant 2

HCID 2631-ButanolHCID 89815411HCID 89815411, compound

Product 1

HCID 178450849HCID 178450849, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
95 °C

Procedure

To a stirred solution of methyl 2-(1,3-dioxo-5-(o-tolyloxy)isoindolin-2-yl)acetate (10.0 g, 30.8 mmol) in n-butanol (206 mL) at 95° C. was added 1 N sodium n-butoxide solution (62.0 mL, 62.0 mmol). The resulting mixture was stirred at 95° C. for 2 hours before cooling to room temperature. The solvent was partially removed and the residue was diluted with EtOAc (200 mL) and 2 N HCl (40 mL). The resulting mixture was stirred vigorously for 15 minutes at room temperature and the precipitation was collected by filtration. The filter cake was washed with H2O and then dried at 70° C. in vacuo to give a yellow solid. The solid obtained was further suspended in EtOAc (300 mL) and the slurry was heated to reflux with stirring for 2 hours. After cooling to room temperature, the precipitate was collected by filtration and then dried in vacuo to give the title compound in 1.6 g. 1H NMR (CDCl3, 200 MHz): δ=10.38 (s, 1H), 8.42-8.32 (m, 2H), 7.43 (s, 1H), 7.34-7.10 (m, 3H), 7.02 (d, 1H, J=7.6 Hz), 4.39 (t, 2H, J=6.6 Hz)), 2.20 (s, 3H), 1.84-1.38 (m, 4H), 0.99 (t, 3H, J=7.2 Hz).

Workup

  1. temperaturebefore cooling to room temperature
  2. customThe solvent was partially removed
  3. additionthe residue was diluted with EtOAc (200 mL) and 2 N HCl (40 mL)
  4. stirringThe resulting mixture was stirred vigorously for 15 minutes at room temperature
  5. customthe precipitation
  6. filtrationwas collected by filtration
  7. washThe filter cake was washed with H2O
  8. customdried at 70° C. in vacuo
  9. customto give a yellow solid
  10. customThe solid obtained
  11. temperaturethe slurry was heated
  12. temperatureto reflux
  13. stirringwith stirring for 2 hours
  14. temperatureAfter cooling to room temperature
  15. filtrationthe precipitate was collected by filtration
  16. customdried in vacuo

Sources & evidence

ORD record
ord-7e1fb692a5a746d2b9d8eff51be96f2f
Source dataset
uspto-grants-2016_08
Patent number
US09409892B2

Reaction notes

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